ORGANIC CHEMISTRY LANEY COLLEGE

CHEM 12B INSTRUCTOR: STEPHEN CORLETT

Dehydration of 2-methylcyclohexanol – Full Report Guidelines

Reading: Experiment 24A (microscale version) and unsaturation tests (p. 214) in Pavia (5th edition); review
Techniques listed under Required Reading. See also Klein, secs. 7.12 and 12.9

Introduction

Heating an alcohol with acid results in the formation of alkenes along with the loss of water (hence, this is
referred to as a dehydration reaction). In our experiment, we will substitute 2-methylcyclohexanol for the 4-
methylcyclohexanol prescribed in Pavia. Our substrate can potentially lead to three unique alkene products.
The product(s) will be removed from the reaction mixture using continuous azeotropic distillation. The organic
product will be separated from the water that co-distills with it, and then dried over anhydrous sodium sulfate.
The product mixture will be analyzed by infrared spectroscopy, gas chromatography-mass spectrometry (GC-
MS), and we will perform the unsaturation tests described in Pavia.

Prelab

Include the usual Name, Date, Purpose, and Outline. The Chemical Equation should depict all three of the
products that can formed from 2-methylcyclohexanol. The prelab write-up must include a detailed Reagent
Table. Be sure to calculate the total theoretical yield of the alkene products (note that all three products have
the same MW). Additionally, you should find and list the boiling points for the three isomeric alkenes that can
be formed. Include a sketch of the reaction apparatus as part of the procedural summary.

Procedure

The experiment is described in Pavia 24A—follow the procedure given except substitute 2-methylcyclohexanol
for the substrate. Our Hickman stills are equipped with the side ports. Will also perform the unsaturation tests
described on page 214. Carefully note the results of the unsaturation tests in your notebook.

To Complete the Experiment – Formal Report (see below)

Items that you need from this experiment to complete the report:

1. FT-IR spectrum
2. GC/MS chromatogram with integrated peaks and the percent report.

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ORGANIC CHEMISTRY LANEY COLLEGE
CHEM 12B INSTRUCTOR: STEPHEN CORLETT

This experiment requires a full write-up, typed report, double-spaced and single-sided. It will involve the
following items (excerpts from the Lab Report Guidelines and Notes):

The Cover Page has the Title, Author, and Affiliation (only)

Title
The title should be descriptive, but not too long (and is the same as used in your notebook) – it should be the
same as the title given on the experimental handout.

Authors
Put your full name first, then any names of partners second (or third).

Affiliation
Indicate where you performed the experiment (e.g., Department of Organic Chemistry, Hauser Laboratory,
University of Colorado, Boulder, Colorado, or in your case, Department of Chemistry, Organic Laboratory, Laney
College, Oakland, CA).

(New page)

Abstract
Probably the hardest part to write, the abstract is a concise statement that tells the purpose of the experiment,
the essential elements of the procedure, and the results. The abstract is only one paragraph in length (and
approximately five sentences). Consider writing this part last!

(A good reference for this is the The ACS Style Guide. Effective Communication of Scientific Information.
Editor(s): Anne M. Coghill, Lorrin R. Garson. 2006 American Chemical Society) See also the provided excerpt
from this guide.

Introduction and Background

Provide the background for the experiment that was performed. Discuss and show all aspects of the relevant
chemical reactions – the expected products, side-products and maybe even another example from the literature
(your textbook, or another book suggested by the instructor). This experiment is somewhat challenging in this
regard, since our standard textbook for the course suggests that a relatively small number of products (3) should
be produced from this particular elimination reaction. Upon closer analysis of the chromatogram (thanks to the
GC/MS), we have observed more products, so you will need to do a little bit of research to find out how to
rationalize the products that were formed.

You should summarize the expected mechanism for the dehydration that was performed and under the
conditions that were used.

Your introduction, however should describe the expected formation of the three most likely alkenes – ones that
might be presented in Klein. Other items to discuss are the experimental conditions that are normally used for
the type of experiment you performed and potential methods to identify your product.

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ORGANIC CHEMISTRY LANEY COLLEGE
CHEM 12B INSTRUCTOR: STEPHEN CORLETT

In this case, provide some background on the conditions used in the dehydration reaction – are the ones used
for this procedure typical?

Show the chemical equation for the reaction – use ChemDoodle (ask if you don’t have it yet) to produce “print-
quality” chemical reactions and insert the graphic into your final report.

Experimental procedure

Provide a step-by-step account of the experiment the way you performed it. It should give all of the vital details
necessary to be repeated by another person (i.e., somebody else should be able to repeat the experiment
without having to ask you any questions). Save any discussion of the quality and quantity of your product for
the Results section (below).

You will need a diagram that shows your apparatus. ChemDoodle has tools to draw it and would be the best
way to include in your report (the default is to hand-draw after you’ve printed your report). The diagram only
needs to show the glassware that was used and how it was assembled. It doesn’t have to be a piece of art, just
needs to clearly show what the parts are - consider that someone else might try to repeat what you did in the
laboratory.

You must write the text in 3rd person and in the past tense (e.g., “The contents of the flask were heated…”
instead of “I heated the flask…” or “The layers were separated and the organic layer was dried with sodium
sulfate, then filtered…”)

Use the procedure given for this lab as the guide, but write it in the correct form – 3rd person, past-tense. If you
modified or adapted the overall procedure (or the instructor added something), it should be noted in your
notebook and reflected in your final procedure. Remember to write the procedure as if you already followed it
– not as if you telling someone else to do it (like Pavia or your instructor does)!

Save analysis of the final product for the next section – Results and Conclusions.

Results and Conclusions

Discuss the results of the experiment. Of course give the percent yield (remember that you weighed the product
before you added the drying agent) - the stoichiometry of the reaction is one mole of alcohol gives one mole of
alkene, whether it is a mixture of isomers or a single alkene. Did you get the product? How do you know it is
the desired product? What are the limitations of your method of analyzing the product?

You should try to account for the formation of each of the products that were observed in the chromatogram.
The mixture is a very difficult one to separate on GC, since the boiling points of each isomer are so similar,
especially ones where the only difference is the placement of the double bond.

The observed order of the products, in order of retention time is: methylcyclohexane; then 3-
methylcyclohexene, 4-methylcyclohexene, and methylenecyclohexane (newly discovered) came at the same
retention time; then 1-ethylcyclopentene and ethylidenecyclopentane came at the same retention time;

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CHEM 12B INSTRUCTOR: STEPHEN CORLETT

followed by the major product, 1-methylcyclohexene; at a much longer retention time, one product that was
found in small concentration was 2-methylcyclohexanone (a clue to the formation of one of the products above).

References

Provide all references to the experiment and the procedure used, including any modifications, and the
information used in your introduction, using the correct bibliographic format for each type of reference. (see
the MLA standards at: https://owl.english.purdue.edu/owl/resource/747/06/ if you are unsure) Usually, your
source will be your laboratory textbook, however give the full correct citation. Since, you will likely do some
investigation into the mechanism of the dehydration (to explain the large number of products), be sure to cite
any internet sources of information.

Final order of assembly:

1. Cover Page
2. Abstract
3. Introduction/Background
4 Chemical Equation
5. Procedure
6. References
7. Laboratory notebook pages

Rough Draft of items 1-6 are due a week after the lab is finished.
Final version due TBD

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